


Persuading Dean

by Angel_in_Conspiracy, Deans_idjit



Category: SPN, Supernatural
Genre: Ass Slap, BDSM, Bi, Bi Sexual, Coming Out, Destiel - Freeform, F/M, Hair Pulling, Rope Bondage, Sex, Sexy, Smut, Supernatural - Freeform, ass, bj, blowjob, boobs, daddy - Freeform, ropes, tease
Language: English
Status: Completed
Published: 2016-12-30
Updated: 2017-01-01
Packaged: 2018-09-13 14:24:37
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 6
Words: 2,652
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9127645
Author URL: https://archiveofourown.org/users/Angel_in_Conspiracy/pseuds/Angel_in_Conspiracy, https://archiveofourown.org/users/Deans_idjit/pseuds/Deans_idjit
Summary: Your sex life drys up along with Dean's providing a tempting idea. Now all you have to do is  persuade Dean. After convincing him, Dean tells you something surprising.





	1. Persuading Dean

**Author's Note:**

> Comment any ideas you have and me and my partner can write a fanfic dedicated and inspired by you!

You are kinky, you like it rough with ropes and cuffs, but Dean, on the other hand, was more classy about things... or so he claimed. You wanted to grab a guys hair and tug on it, be slapped on the ass so hard you bruised, and gagged to the point of submission. You and Dean weren't dating and had never had sex, both single and best friends. You talked about everything with Dean and surprisingly he was a good 'therapist'.  
One afternoon you and Dean were talking while sitting and drinking in the kitchen in the bunker. You were dwelling in your singleness and self loathing. Somehow the conversation turned to how both of you haven't had sex in so long and just wanted a fuck.  
"You know Dean, it's been a hell of a long time since I've had sex, and you haven't had sex in a long time either. I was thinking maybe we could hook up or something." You say casually.  
"Us, have sex. Ha. No thanks sweetheart; I don't wanna be tied up and rough housed. I don't need that shit to get off."  
"Aww c'mon, Dean. It'll be fun." You plead as you do a sexy little dance for Dean. He was clearly contemplating having sex with you but determined you shouldn't in saying, "Look Y/N, you are my best friend and you are beautiful, probably one of the hottest girls I've seen," Dean says sweetly, smirking. "But our friendship is not something I wanna fuck up. Now that Sammy is out hunting on his own more, I need someone with me where it won't be awkward."  
"Yeah... I guess I get it." Sipping your beer, you resolved you were gonna get Dean for yourself. You just had to figure out a plan to get him in your bed, or on the couch, or the kitchen counter, or the floor. You didn't care where, you just wanted him.


	2. Stripper days

**Summary for the Chapter:**

> You surprise Dean with a sexy dance you learned back in your stripper days.

Once you determined you were going to have Dean, you began to tease him the only ways you knew how. Thankfully your former stripper days came in handy for this part. A few hours after your talk, you put the stripper pole to use. You went to your room, picking the sexiest lingerie you had and put it on. You admired yourself in the mirror and went to the pole. On one of Dean's drunken purchases he had bought a stripper pole, not knowing your experience. Dean was drinking alone and doing some research for Sammy as usual, so you went to help. You strutted through the hallways, swaying your hips as you walked in your high heels paired with black lace bra and panties. Walking in the room you come up behind Dean and put your arms on his shoulders, moving them slowly down his chest as your breasts graze the back of his head. You say in your sexy voice, "You know that stripper pole you bought might see some use tonight." Confused and still focused on his work, Dean says,"What for?" "Well I haven't told you this but I have some experience in the stripper industry." You back up so that Dean can turn around and see you. He still hasn't connected the dots because he is so focused on this case. He backs up and turns around, eyes becoming wide. He is speechless. Then he comes back from the cloud nine he was on and says, "didn't we already discuss this Y/N? A friends with benefits relationship will not be good for our friendship" "You're loss babydoll," you say as you swiftly turn, revealing your ass. Knowing butts were Dean's weakness you walked away swaying side to side. You were almost to the door when Dean says "Wait, maybe we can make an arrangement." Turning back around, but still going towards the hall, you turn the corner. Then pop your head back around the corner to lure Dean to follow you. "You coming?" Dean hastily stands up and walks quickly in your foot steps, trying to keep up.


	3. Blow me away

You strut down the hall, Dean hot on your trail. He couldn't keep his eyes off of your ass as you walked. Right before getting to the stripper pole you grab a chair for Dean. You give him a gentle shove so that he sits down and you get so close to his face your lips almost touch. "You might wanna loosen your pants, cause they're about to get real tight in the crotch area." You wink and walk up the the pole. Dean was getting aroused by your teasing but tried to keep his composure.  
You walk to the pole and grab it. You swing around dropping lower and lower. And when you stand up you put your ass less than 12 inches in front of Dean's face. He was trying to keep it cool, but he was clearly turned on. You do a few more moves even sexier than before when Dean says, "Why don't you move the show a little closer to me," implying he wants a lap dance. You get off the pole and onto your knees, slowly crawling to Dean like a wild animal. You make it to Dean and come up to kiss him. His kisses so sweet and sensual. You never knew how much you needed his kisses till you felt them. His kiss made time slow down, his lips so soft and the scruff of his face barely grazing your cheeks. His hand grabs your face pulling you closer to him. The faint smell of beer and musk fills the room, enchanting you both. You feel Dean's cock straining against his pants, knowing he was getting turned on. You undo his belt while still kissing him and begin to pull down his pants. You already new Dean was going to be big, but you never thought he would be 8 inches of perfection with just the right thickness. Big enough to fill you up and then some, but not too big for a blow job. You begin sucking his cock, making you wet and even more turned on. Your mouth and hands work in tandem pumping his cock so good. "Fuuuck," Dean groans loudly. "You were right this is amazing."  
"Never thought Dean Winchester would ever fess up to being wrong." You continue to pump his cock.  
You get up off your knees and unclip your bra, exposing your tits to Dean. "Man, we should've done this sooner" Dean says.


	4. Strange interruptions

He throws you over his shoulder and carries you to his room. He tosses you on the bed and ties you down. He kisses you while hovering over you and pulls down your panties. He leaves a trail of kisses down your body all the way down to your aching core. He peppers kisses on the inside of your thighs and around your vagina, teasing you.   
"Dean pleaaase," you beg. "I haven't been fucked in so long. I just want you." He sucks your clit into his mouth, teasing you with the tip of his tongue. He releases it and plunges his tongue deep inside you. He moans as he tastes you, sending vibrations trough your body. The coil in your abdomen begins to tighten. You arch your back and push back into his face, begging for more. Constant waves of pleasure course through you. Your moans only encourage Dean to keep going. The coil finally snaps and you are coming. Your body tenses and you squeeze your eyes shut, legs clenching around his head through your orgasm. You are finally let up from the intense orgasm that Dean worked you through, uttering words of praise the entire time. Dean looks pleased with himself as he travels back up, grabbing at your breasts, to kiss you. You breathlessly whisper, "Oh... god yes." He smiles and kisses you again when suddenly Cas appears in the room. Cas looks shocked at what he sees, and somewhat jealous. "Oh gosh, sorry Y/N, I didn't know you where gunna be, well ya know." You let out a screech and Dean covers you, as you are still tied up. Dean pulls up his boxers and walks Cas out of his room. "What do you need Cas? I'm kinda in the middle of something. Or more like some one I guess. Ha ha," he says in his cute proud of himself laugh.  
"I just had some news on the vampire case, but it can wait." Cas says this almost angrily and stops off out of the bunker.


	5. The best sex

**Summary for the Chapter:**

> After amazing sex with Dean he wants to come clean.

"Wonder what that was about." Dean mumbles, even though he knew what it was about. He walks back in the room and smiles at the sight of you all tied up. "While you're up why don't you grab the anal beads for me." You say. He starts for his dresser and stops saying, "wait how did you know I have those?" You smirk and say, "well, I was looking for a book for a case and I found it in a drawer. And what happened to you not being kinky? You say you don't need that shit, but you have anal beads for yourself." Dean seemed a little embarrassed so you reassured him, "I like that you have anal beads. It's just another turn on." Dean's goes and grabs the beads then throws them on the bed. He walks to the bed and climbs on top of you and kisses you. He kisses your neck and cheeks while purring lube on the beads the beads. He then slowly pushes them in one at a time. You moan with lust. He shoves his tongue in your mouth then breaks away to finally take off his shirt. His body was perfect, muscular, but not ripped; large, but not bulky. Dean's erection hardens further if that's even possible, and he puts the gag back in your mouth. He teases you with his dick, hearing you moan through the gag. Dean finally begins to push in slowly until he is fully sheathed inside you. He thrusts deep and powerful. Dean moans and grunts consistently, deep, husky grunts. It makes you more wet to hear him making these sounds of pleasure. It still isn't kinky enough for you. "Dean... Dean... fuuck." You say through the gag, "Get the clamps." You are of course referring the the nipple clamps he has. "Damnit, how did you know I had those too?"   
You give him a sexy look. He slows down and reaches over and grabs the claps. He starts the put them on you but you say, "No no daddy, I want them on you." Dean smiles and puts them on himself. He then flips you over and smacks your ass. "Oh daddy yes. You know how much I like it rough, mmm." He starts thrusting faster and harder, pounding into you. You can already feel signs of your orgasm creeping up on you. With each thrust comes the wet slap of skin on skin. This was amazing, what you'd always dreamed of, the hottest person you'd ever seen fucking you. "Mmm big boy want you to fuck me in the ass." Dean takes his cock out and rubs lube over your hole and his dick. He takes out the anal beads and slowly inserts his cock. When things are in your ass it has a unique sensation.  
"Ohh fuck yes Winchester." You suddenly cum at a surprising intensity. Dean works you through your orgasm, continuously thrusting into you. "Fuuuck yes" Dean says as he takes his cock out of you. He unties you and takes the gag out, so you can finish him off. In the heat of the moment you turn around and put more lube on the anal beads. You push them into Dean's ass and jerk him at a fast pace, making him cum all over your face and breasts. He grunts and moans during his orgasm. You pump his cock a few more times and rub the cum all over your breasts. "You like that daddy?" "Best friggin sex I've ever had." A few minutes later of lying around, Dean says "I have to tell you something important"


	6. Destiel

**Summary for the Chapter:**

> After Dean confesses the truth, he finds his true love.

"What are you talking about Dean? Just hold on and let me take a shower this sounds serious," You says with a confused look on your face. You go and take a shower, pondering the whole time what he might say to you. You think 'maybe he has a girlfriend. No no Dean has no time to have a girlfriend. Maybe he has caught feelings, or maybe he is going to talk about his kinks. Haha Dean is so mysterious, he should be the 8th wonder of the world,' Your thoughts continue to wonder as you shower. You try to shower quickly, but you get lost in your own thoughts and take a long while. You worry Dean has fallen asleep so you clunk around trying to keep him awake. You dry off feeling refreshed and ready to talk. You come out and Dean was sitting their looking tired and worried. The bed was oddly covered in a towel. "What's under the towel Dean?" Dean looks ashamed so you repeat, "Dean, what's under the towel?" This time more forcefully. He uncovers the towel and he shows you at least 15 different sex toys. Some dildos, cock rings, clamps, whips and an assortment of other things. "I think it is important that you know... I'm bi-sexual." You slowly walk over and sit on the bed. "Dean, I don't give a flying fuck if you're gay, straight, male, Asian, female, pan, black, white, short, midget or bi, as long as you are you." Dean still didn't look relived. "Y/N there's more. I have feelings for Cas." You looked more surprised than before, "Okay, umm...that explains him stomping out of here. So..." You sit there a minute trying to come up with words, but you can't. 'It's weird,' you think. 'The guy I just fucked is bi and has feelings for an angel that is a dude and just flew in on us.... that's normal'. "So Dean what do you wanna do about it then?"  
"Well, I think we should talk to Cas about it." You both begin praying that Cas will show up, when he appears and says, "What do you 'love birds' want? I could be off fucking other people.. like Dean." He says angrily, "He just goes around fucking everything he feels like, girl or guy doesn't matter." He walks back and forth, using his hands to talk and show expression as he bitches.  
"Common Cas chill out, I'm sorry, I didn't know you felt the sa-" Cas cuts you off, beginning to ramble and pace back and forth. "Who says I feel the same way? Maybe, just maybe I don't like the fact you're a man whore and instead of focusing on the real problems you fuck other people WHY FOR CHUCKS SAKE TELL ME!!! I mean when's the lasttimeyou'vebeenhunting dean, huh? Weeks maybe months. Instead you're herehavingsex with women. Dean you're better than this, there is moretoyourlife than just meaningless sex!" You are mortified. Dean is crying, though he tries not to show it. "I'M SORRY OKAY I LOVE YOU!" Dean yells, half in anger half in tears. All anger fades from Cas's face. Cas hurries to Dean and kisses him. You heart melts with happiness, and your eyes fill with tears. You never loved Dean, not like Cas does. You only wanted him for the fuck. God he was gorgeous and perfect, but not for you. He was your best friend, nothing more. They kissed long and desperate, neither coming up for air. Neither of them were turned on. Not because they didn't find each other attractive, but because it was pure love, not lust. Something you longed for, but couldn't have.


End file.
